Chocolatey

What do you like best?

Chocolatey offers version control for our env as well as a simplification of deploying software to non-admin users. It provides a well developed GUI interface for users and a solid cmd line for more technical users.

One of the better things it offers is powershell scripting, you can follow the chocolatey rules, or just use it to deploy a powershell script when needed. It has a stdlib which has it's own functions, or you can write your own - which my org has. We use chocolatey for mass deployment and version control in my company.

The developers have/are introducing a reporting and central control console, but it's in beta/early intro and while our company will pick it up eventually, we use pdq inventory for the moment for reporting details.

The support staff are top-notch and really know what they are doing. It can be difficult to understand some of the documentation as it is very technical. I've never had a problem with support breaking down the concepts for me when I don't understand them.

There is a free version, and a paid-for Enterprise version. I dont know anything about the free version, but the enterprise version includes a background service. This service will essentially hide everything from the user. While your applications need to be packaged well, and not say leaving a prompt hanging out there waiting for input, any windows/etc that could mess with install are hidden. Yes, sometimes silent installs will suppress these, sometimes applications aren't written that well however and chocolatey covers you in that case.

There are growing pains with the product as they support new interfaces being developed, support has never let me down however. There will always be the occasional quirk, and there are definately some bugs in certain packages, however with powershell there is a variety of ways things can be re-tried. The support staff works through issues we have and works closely with developers. It is not uncommon for your particular issue to be worked into a new update once identified fairly quickly, and if there isn't a release soon they do have beta offerings.

While I can't comment on the free version of chocolatey as I simply dont have knowledge of it, I can fully recommend the enterprise product. Make sure you invest significant time to training your application packagers to learning it, and perhaps working with the support staff and it will pay off very well for you. While it certainly isn't something you just click-through and your up and running in a few minutes, if you have a complex environment it can help simplify for your users.

What do you dislike?

The documentation on the site is not for newcomers. It's very technical and not an easy read or particularly well organized. Chocolatey is pushing to become a full enterprise solution, but at the moment I feel you would be best jumping in if you are a intermediate to advanced application packager intimately familiar with powershell. I jumped in as a bit further along than a novice application packager, and my skills in working with chocolatey for over a year have definately jumped from novice to intermediate. You will definitely learn things working with the product, and the support staff are definitely top-notch. Making well organized guides that are more entry-level and user-friendly would greatly enhance the viability of the product and bring it to a whole new userbase.

Chocolatey has it's rules to follow, and as a newcomer getting over that hump of learning what they are and following them every time is a steep learning curve. You could use canned packages they offer, however my org tends to make every package largely from scratch. Once you get the process down however it becomes a serious tool for automation.

In order to develop packages, it takes on average 2-4 hours to build, test, and run through a git process to build packages. On more advanced one's it's taken me up to 20-ish hours. Chocolatey isn't something to hand development of packages to a level 1 helpdesk person, you really need to have staff that can understand application packaging and powershell to make it work. For deploying packages however the process could not be simpler and anyone can do it.

The GUI is very nice, but since version .11 (which is where I started at) it's always been a little flakey. With recent upgrades to 0.9.1 it's very flakey, and sometimes just doesnt' work. Our userbase prefers the GUI and I can see why, it's a nice looking one. However the CMD line is always very solid and we offer the GUI to our users as a 'nice to have, but dont count on it'. It's always being worked on/upgraded, but there's a lot of work to do before I would consider the GUI functional and stable. Stick to the CMD line and you can't go wrong.

Recommendations to others considering the product:

If you have skilled application packagers it can be so incredibly useful. If you do not, or have novice packagers then allot significant time for them to learn the product and it will be rewarded.

What problems are you solving with the product? What benefits have you realized?

We have a multi-tier solution for application management. We use chocolatey for application management. With those applications being in a central location we can install them on client machines, and we use PDQ Deploy to push them out. We also use MDT (Microsoft Deployment Tools, the deployment mechanism for SCCM) to push out the chocolatey packages. Essentially we have meta packages which are a entire listing of packages that are installed. You select from the MS GUI menu which metas to install, and after the chocolatey install it's installing all those programs, where typically you would have to update the packages within MDT and PDQ Deploy, it gives a centralized place for us.